Diddy Blows Kisses to His 6 Kids and Mom in Courtroom at Bail Hearing

Sean “Diddy” Combs was seen blowing kisses and smiling at his family during his latest bail hearing on Friday, November 22.

Us Weekly was in the New York City courtroom as the rapper, 55, showed affection to his mother, Janice Combs, and six children: Justin, 30, Christian, 26, Quincy Brown, 33, Chance, 18, and twins D’Lila and Jessie, 17. (His youngest, 23-month-old daughter Love, was not present.)

The children wore all black (with the exception of the twins, who wore identical white coats with matching halo-esque headbands).

Diddy wore his beige prison jumpsuit but entered the room without shackles. He immediately looked around for his family, smiling and waving as soon as he located them in the courtroom. He then blew kisses and mouthed “I love you” before the proceedings began. Diddy’s defense team pointed out the family's presence in opening statements, noting, "They traveled a great distance to be here.”

A decision on whether Diddy will be allowed a release on bail is expected next week.

A Timeline of Diddy’s Legal Troubles and Accusations: From Cassie Lawsuit to Multiple Arrests

Earlier this month, the Associated Press reported that Diddy, 55, filed a new request on November 8 to be released from Brooklyn’s Metropolitan Detention Center, claiming that he should be allowed to prepare for his May 2025 trial outside of prison due to changed circumstances and new evidence.

In the filing, Diddy’s lawyers proposed a “far more robust” $50 million bail package with stipulations such as full-time security monitoring, home detention and restrictions on his ability to contact anyone but his legal team.

As part of the agreement, Diddy’s attorneys suggested that he would not have internet or phone access and would be allowed a pre-approved visitor list of select family members. USA Today also reported that Diddy would have to surrender passports that belonged to him and his family.

Diddy’s legal team went on to cite new evidence that “makes clear that the government’s case is thin” against him. His attorneys claimed that the evidence refuted the government’s claims that a 2016 video of Diddy assaulting then-girlfriend Cassie occurred during a “Freak Off,” where he allegedly coerced female victims to participate in “elaborate and produced sex performances.”

Diddy’s Ups and Downs Over the Years: Name Changes, Lawsuits, Home Raid and More

However, prosecutors argued in a November 15 legal motion that Diddy’s bail request should be denied, alleging that he tried to obstruct the investigation while in jail. In court documents obtained by CNN, Diddy was accused of orchestrating social media campaigns “aimed at tainting the jury pool” and contacting “witnesses through third parties.”

Diddy’s attorneys subsequently claimed in a Monday, November 18, motion that his rights were violated during a search of his jail cell, while Assistant U.S. Attorney Christy Slavik alleged that Diddy wrote notes on his calendar about “paying off witnesses and finding dirt on victims,” according to NBC News. The following day, U.S. District Judge Arun Subramanian ruled that prosecutors were required to “get rid of copies” of the notes, but the court would “keep the papers” as the defense and prosecution prepared to “submit briefs about the raid” in the weeks ahead.

Prior to the most recent request, Diddy had already been denied bail on three separate occasions. He has been behind bars since his September arrest for sex trafficking and racketeering charges, to which he pleaded not guilty.

If you or someone you know has been sexually assaulted, contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673).

Reporting by Molly McGuigan